반응 #474558

반응 방정식

5-Bromo-3-(2,2-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

1,4-dioxane

3-Furanylboronic acid

K2CO3

→

title compound

수율 26.0%

3-(2,2-Dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-furanyl)-1H-indole-7-carboxamide

수율 26.0%

용매

water

반응 조건

후처리

1. 1
   기타Argon was bubbled in the mixture for 10 min
2. 2
   기타argon was bubbled another 10 min
3. 3
   기타The vial is sealed
4. 4
   기타The reaction was evaporated
5. 5
   기타to remove most of the dioxane
6. 6
   기타The residue was partitioned between ethyl acetate and water
7. 7
   기타The layers were separated
8. 8
   건조the organic layer was dried (MgSO4)
9. 9
   기타the solvent was removed under vacuum
10. 10
    workup.DISSOLUTIONThe residue was dissolved in the minimum amount of MeOH and EtOAc
11. 11
    세척eluting with 2 mL of MeOH
12. 12
    기타The solvent was removed under vacuum
13. 13
    workup.DISSOLUTIONthe residue was dissolved in 1-2 mL of DMSO
14. 14
    기타purified on a Gilson HPLC
15. 15
    농축The desired fractions were concentrated

실험 절차

5-Bromo-3-(2,2-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (80 mg, 0.20 mmol) was placed in a microwave vial and dissolved with 1,4-dioxane (2 mL) and water (1 ml). 3-Furanylboronic acid (44.8 mg, 0.401 mmol) and K2CO3 (83 mg, 0.60 mmol) were added. Argon was bubbled in the mixture for 10 min with stirring. PdCl2(dppf) (4.83 mg, 0.01 mmol) was added, and argon was bubbled another 10 min. The vial is sealed and heated in a microwave for 5 min at 100° C. on high absorption. The reaction was evaporated to remove most of the dioxane. The residue was partitioned between ethyl acetate and water. The layers were separated, the organic layer was dried (MgSO4), and the solvent was removed under vacuum. The residue was dissolved in the minimum amount of MeOH and EtOAc, and was run through a thiol-SPE cartridge eluting with 2 mL of MeOH. The solvent was removed under vacuum, and the residue was dissolved in 1-2 mL of DMSO, and purified on a Gilson HPLC. The desired fractions were concentrated, giving 22 mg (26%) of the title compound.

출처